Product Name

  • Name

    1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose

  • EINECS
  • CAS No. 2595-05-3
  • Article Data76
  • CAS DataBase
  • Density 1.214 g/cm3
  • Solubility
  • Melting Point 73-77oC
  • Formula C7H9N3O2
  • Boiling Point 362.753 °C at 760 mmHg
  • Molecular Weight 260.287
  • Flash Point 173.187 °C
  • Transport Information
  • Appearance
  • Safety 22-24/25-36/37-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2595-05-3 (1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose)
  • Hazard Symbols Xi
  • Synonyms Allofuranose, 1,2:5,6-di-O-isopropylidene-, a-D-(7CI,8CI);1,2:5,6-Di-O-isopropylidene-a-D-allofuranose;1,2:5,6-Diacetone-D-allofuranose;Diacetone-D-allofuranose;(3aR,5S,6R,6aR)-5-[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (non-preferred name);
  • PSA 66.38000
  • LogP 0.37520

Synthetic route

2,2,2-Trichloro-acetimidic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

2,2,2-Trichloro-acetimidic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 2h; Ambient temperature;100%
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose
2847-00-9

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h;96%
With sodium tetrahydroborate In ethanol; water at 0℃; for 1h;90%
With sodium tetrahydroborate In ethanol; water at 20℃; for 3h; stereoselective reaction;84%
3-O-tetrahydropyranyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
226943-46-0

3-O-tetrahydropyranyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
With water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 75℃; for 0.5h;91%
With iodine In methanol at 20℃; for 1h; acetal cleavage;90%
3-O-(4,4'-dimethoxytrityl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
226943-66-4

3-O-(4,4'-dimethoxytrityl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
With iodine In methanol at 20℃; for 1h; ether cleavage;88%
With water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 75℃; for 0.25h;85%
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃;
Stage #2: With sodium tetrahydroborate In methanol at 0℃;
85%
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With dipyridinium dichromate; acetic anhydride In dichloromethane
Stage #2: With sodium tetrahydroborate In ethanol
83%
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride In dichloromethane at -65 - 20℃;
Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 1h;
82%
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose
2847-00-9

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

A

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

B

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
With sodium tetrahydroborate In methanolA 4.49 g
B n/a
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

C6H6O2(OBn)3(OPiv)SP(S)(OEt)2

C6H6O2(OBn)3(OPiv)SP(S)(OEt)2

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CrO3; Ac2O; pyridine / CH2Cl2 / 1 h / 0 °C
2: 8.0 g / NaBH4 / ethanol / 0.5 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: CrO3; Ac2O; pyridine / CH2Cl2 / 2.5 h / 0 - 20 °C
2: 4.49 g / NaBH4 / methanol
View Scheme
Multi-step reaction with 2 steps
1: 85 percent / PCC; 3 Angstroem molecular sieves; neutral alumina / CH2Cl2 / 15 h / 20 °C
2: 96 percent / NaBH4 / aq. ethanol / 2 h / 0 - 20 °C
View Scheme
alpha-D-glucopyranose
492-62-6

alpha-D-glucopyranose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 32 percent / ZnCl2; H3PO4 / 30 h / 20 °C
2: 85 percent / PCC; 3 Angstroem molecular sieves; neutral alumina / CH2Cl2 / 15 h / 20 °C
3: 96 percent / NaBH4 / aq. ethanol / 2 h / 0 - 20 °C
View Scheme
D-Glucose
2280-44-6

D-Glucose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 68 percent / ZnCl2; aq. H3PO4 / 36 h / 20 °C
2: 91 percent / pyridinium dichromate; acetic anhydride / CH2Cl2 / 4 h / 75 °C
3: 90 percent / NaBH4 / ethanol; H2O / 1 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: phosphoric acid; zinc(II) chloride / 36 h / Reflux
2: dipyridinium dichromate; acetic anhydride / dichloromethane / 2 h
3: sodium tetrahydroborate / ethanol / 2 h
View Scheme
Multi-step reaction with 2 steps
1: zinc(II) chloride; phosphoric acid / acetone
2: acetic anhydride; pyridinium chlorochromate / dichloromethane
View Scheme
Multi-step reaction with 3 steps
1: zinc(II) chloride; phosphoric acid
2: acetic anhydride; dipyridinium dichromate / dichloromethane
3: sodium tetrahydroborate / ethanol
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid
2: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice
3: sodium tetrahydroborate; ethanol / Cooling with ice
View Scheme
D-gulose
4205-23-6

D-gulose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc(II) chloride / Inert atmosphere; Schlenk technique
2: chromium(VI) oxide; acetic anhydride; pyridine / Inert atmosphere; Schlenk technique
3: sodium tetrahydroborate / ethanol; water / 3 h / 0 °C / Inert atmosphere; Schlenk technique
View Scheme
3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside
4613-62-1

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / -78 - 20 °C
2: sodium tetrahydroborate; water / ethanol / 1 h / 0 °C
View Scheme
D-glucose
50-99-7

D-glucose

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid
2: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / -78 - 20 °C
3: sodium tetrahydroborate; water / ethanol / 1 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: copper(II) sulfate / Acidic conditions
2: acetic anhydride; PDC
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid
2: phosgene; triethylamine / dichloromethane / 1.5 h / -78 - 20 °C
3: sodium tetrahydroborate; ethanol / water / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: zinc(II) chloride; phosphoric acid / 15 - 30 °C / Large scale
2: potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite; sodium hydrogencarbonate / water; ethyl acetate / 0 - 35 °C
3: sodium tetrahydroborate / water / 10 - 15 °C
View Scheme
Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2-O-isopropylidene-α-D-allofuranose
4495-04-9

1,2-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With water; acetic acid at 20℃; for 8h; regioselective reaction;100%
Stage #1: Diacetone D-glucose With carbon tetrabromide In methanol for 0.5h; Irradiation;
Stage #2: In methanol at 20℃; for 14.5h;
90%
With silica supported polyphosphoric acid In acetonitrile at 55℃; for 0.5h;82%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose
55951-90-1

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose

Conditions
ConditionsYield
With pyridine In dichloromethane at -30℃; for 0.75h;100%
With pyridine at 0 - 20℃; Inert atmosphere;95%
With pyridine at 0 - 20℃; for 3.5h;92%
5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
85920-63-4

5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

(1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl) 3-oxobutanoate
342003-61-6

(1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl) 3-oxobutanoate

Conditions
ConditionsYield
In toluene for 8h; Heating;100%
benzyl bromide
100-39-0

benzyl bromide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose
22331-21-1

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 8h;100%
Stage #1: Diacetone D-glucose With sodium hydride In acetonitrile; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide In methanol; acetonitrile; mineral oil at 0℃; for 4.5h;
90%
With sodium hydride60%
benzoyl cyanide
613-90-1

benzoyl cyanide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate
29474-73-5

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0℃;100%
With triethylamine In acetonitrile at 20℃; for 15h;
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane
378238-89-2

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 18h;99%
binaphthol chlorophosphite
137156-22-0, 171878-71-0, 155613-52-8

binaphthol chlorophosphite

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

4-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene

4-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene

Conditions
ConditionsYield
With triethylamine In toluene for 16h;99%
With triethylamine In toluene for 16h;98%
acetic anhydride
108-24-7

acetic anhydride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
29474-72-4

3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With iron(III) sulfate at 20℃; for 6h;99%
With pyridine at 20℃;
With pyridine
pivaloyl chloride
3282-30-2

pivaloyl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-O-(2,2-dimethylpropanoyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

3-O-(2,2-dimethylpropanoyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 72h;99%
α-chlorophenylacetyl chloride
2912-62-1

α-chlorophenylacetyl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl α-chloro-α-phenylacetate

1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl α-chloro-α-phenylacetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;99%
2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-O-(2-naphthylmethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
956485-06-6

3-O-(2-naphthylmethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0℃;99%
With sodium hydride In N,N-dimethyl-formamide for 1.16667h; Cooling with ice;99%
With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice;99%
2-bromomethylnaphthyl bromide
939-26-4

2-bromomethylnaphthyl bromide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

C23H28O6

C23H28O6

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice;99%
2-Bromopropionic acid
598-72-1

2-Bromopropionic acid

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl α-bromopropionate

1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-O-yl α-bromopropionate

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 3h;98%
Diacetone D-glucose
2595-05-3

Diacetone D-glucose

(4-tert-butylphenyl)methanesulfonyl chloride

(4-tert-butylphenyl)methanesulfonyl chloride

(4-tert-Butyl-phenyl)-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
412021-21-7

(4-tert-Butyl-phenyl)-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 24h;97%
isobutyryl chloride
79-30-1

isobutyryl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-O-(2-methylpropanoyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

3-O-(2-methylpropanoyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 2h;97%
hexadecylamine
143-27-1

hexadecylamine

2,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
58851-58-4

2,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

C26H41O7PS2*C16H35N

C26H41O7PS2*C16H35N

Conditions
ConditionsYield
Stage #1: 2,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide; Diacetone D-glucose In benzene at 20℃; for 1h; Inert atmosphere;
Stage #2: hexadecylamine In benzene at 20℃; for 1h; Inert atmosphere;
97%
butyryl chloride
141-75-3

butyryl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-O-butanoyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
120255-67-6

3-O-butanoyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 2h;96%
(Z)-2-methyl-2-butenoic anhydride
94487-74-8

(Z)-2-methyl-2-butenoic anhydride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-angeloyl-1,2:5,6-O-isopropylidene-allofuranose
1417986-37-8

3-angeloyl-1,2:5,6-O-isopropylidene-allofuranose

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 0.5h;96%
Diacetone D-glucose
2595-05-3

Diacetone D-glucose

(3S)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose
32785-94-7

(3S)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose

Conditions
ConditionsYield
Stage #1: Diacetone D-glucose With sulfuryl dichloride In dichloromethane at -5 - 0℃; for 0.666667h; Inert atmosphere;
Stage #2: With 1,2,3-Benzotriazole In dichloromethane at 20℃; for 6.5h; Inert atmosphere;
96%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose
55951-93-4

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose

Conditions
ConditionsYield
Stage #1: Diacetone D-glucose With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere;
96%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-O-[(tert-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
403737-31-5

3-O-[(tert-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 18h;95%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;94%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation;
benzoyl chloride
98-88-4

benzoyl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate
29474-73-5

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

Conditions
ConditionsYield
In pyridine at 20℃; for 6h; Acylation;95%
With pyridine at 20℃; for 20h;90%
With pyridine at 0 - 20℃; Inert atmosphere;90%
With pyridine In dichloromethane at 0℃; for 1h;
In pyridine
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose
3253-75-6, 13964-21-1, 19131-06-7, 23344-48-1, 26597-75-1, 28140-21-8

1,2,5,6-di-O-isopropylidene-3-O-(p-toluenesulfonyl)-α-D-allofuranose

Conditions
ConditionsYield
With pyridine at 20℃; Tosylation;95%
With pyridine91.6%
With pyridine at 0 - 20℃;66%
With pyridine; dmap at 20℃; for 48h;57%
With pyridine; dmap In dichloromethane at 0 - 20℃; for 12h; Product distribution / selectivity;
Diacetone D-glucose
2595-05-3

Diacetone D-glucose

3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose
14049-05-9

3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose

Conditions
ConditionsYield
With pyridine In dichloromethane; toluene at -78 - 40℃; for 168h;95%
With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; toluene at -78 - 40℃; for 168h;95%
With potassium fluoride; 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; N-ethyl-N,N-diisopropylamine In toluene at 80℃; for 16h; Inert atmosphere;83%
2-chloroethyl methyl ether
627-42-9

2-chloroethyl methyl ether

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropyliden-3-O-(2-methoxyethyl)-α-D-allofuranose
553664-29-2

1,2:5,6-di-O-isopropyliden-3-O-(2-methoxyethyl)-α-D-allofuranose

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 55℃; for 7.5h;95%
allyl bromide
106-95-6

allyl bromide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

1,2:5,6-di-O-isopropylidene-3-O-allyl-α-D-allofuranose
33746-39-3

1,2:5,6-di-O-isopropylidene-3-O-allyl-α-D-allofuranose

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 25℃; for 2h;95%
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dichloromethane; water at 23℃; for 5h;92%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h;
With tetra-(n-butyl)ammonium iodide; sodium hydroxide In dichloromethane; water at 23℃; for 5h;
isopropyl 2-bromoacetate
29921-57-1

isopropyl 2-bromoacetate

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

[(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-acetic acid isopropyl ester

[(3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-acetic acid isopropyl ester

Conditions
ConditionsYield
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In tetrahydrofuran at 0 - 20℃; for 48h;95%
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
149707-75-5

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
1138333-94-4

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 4h; Molecular sieve; Inert atmosphere;94%

1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose Chemical Properties

 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is called for 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranoside ; Diacetone-alpha-D-all ; 5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-D][1,3]dioxol-6-ol ; Diisopropylideneallofuranose ; Diacetoneglucose ; ZINC04262105 ; CID7157054 ,and so on. 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is white solid.

IUPAC Name: (3aR,5S,6R,6aR)-5-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
CAS: 2595-05-3
Molecular Formula: C12H20O6
Molecular Weight: 260.28
Molecular structure:
Melting point:  73-76 °C(lit.)
Storage temp.:  2-8°C
H bond acceptors: 6 
H bond donors: 1 
Freely Rotating Bonds: 2 
Index of Refraction: 1.483 
Molar Refractivity: 61.24 cm
Molar Volume: 214.3 cm
Polarizability: 24.28 10-24cm3 
Surface Tension: 43.6 dyne/cm 
Density: 1.214 g/cm3 
Flash Point: 173.2 °C 
Enthalpy of Vaporization: 70.46 kJ/mol 
Boiling Point: 362.8 °C at 760 mmHg 
Vapour Pressure: 9.94E-07 mmHg at 25°C 

1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose Uses

 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is commonly used as chemical reagent.

1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose Safety Profile

Hazard Codes:  Xi
Risk Statements:  36/37/38 (36/37/38:  Irritating to eyes, respiratory system and skin)
Safety Statements:  22-24/25-36/37-26 (22:  Do not breathe dust 24/25:  Avoid contact with skin and eyes 36/37:  Wear suitable protective clothing and gloves 26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
WGK Germany:  3
F:  21

1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose Specification

Removal in wastewater treatment of 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) can be stated as follows:
Total removal:2.71  percent
Total biodegradation:0.10  percent
Total sludge adsorption:2.62  percent
Total to Air:0.00  percent
(using 10000 hr Bio P,A,S)

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